Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

4. Alkanes and Cycloalkanes

Naming Cycloalkanes

Organic Chemistry

4. Alkanes and Cycloalkanes

Naming Cycloalkanes

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4:05 minutes

Problem 3

Textbook Question

(•••) Correct the following incorrect names using standard IUPAC nomenclature. [Draw a compound that corresponds to the incorrect name, and then rename it.](e) 2,6-diethyl-1-methylcycloheptane

Verified step by step guidance

Draw the structure of the compound based on the given incorrect name, 2,6-diethyl-1-methylcycloheptane. Start with a cycloheptane ring (a seven-membered ring) as the parent structure. Add a methyl group at position 1 and ethyl groups at positions 2 and 6.

Analyze the substituents and their positions. According to IUPAC rules, the numbering of the ring should minimize the locants of the substituents. Reevaluate the numbering to ensure the lowest possible set of locants for the substituents.

If necessary, renumber the ring to achieve the correct locants. For example, if the current numbering does not provide the lowest set of locants, start numbering from a different position on the ring.

Reassess the substituents' alphabetical order. In IUPAC nomenclature, substituents are listed in alphabetical order, ignoring prefixes like di-, tri-, etc., but considering the base name of the substituent (e.g., 'ethyl' comes before 'methyl').

Combine the corrected locants, substituents, and parent name into the proper IUPAC name. Ensure that the name reflects the correct structure and follows all IUPAC rules for nomenclature.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

IUPAC Nomenclature

The International Union of Pure and Applied Chemistry (IUPAC) nomenclature provides a systematic method for naming organic chemical compounds. It involves rules for identifying the longest carbon chain, determining the position of substituents, and ensuring that names reflect the structure of the molecule accurately. Understanding these rules is essential for correcting incorrect names and ensuring clarity in chemical communication.

Cycloalkanes

Cycloalkanes are saturated hydrocarbons that contain carbon atoms arranged in a ring structure. The naming of cycloalkanes follows specific conventions, where the prefix 'cyclo-' is added to the name of the alkane corresponding to the number of carbon atoms in the ring. Recognizing the structure of cycloalkanes is crucial for accurately interpreting and renaming compounds like cycloheptane.

Substituent Positioning

In organic nomenclature, substituents are groups attached to the main carbon chain or ring. Their positions are indicated by numbers that reflect their location on the parent structure. Correctly identifying and numbering substituents is vital for accurate naming, as it ensures that the name conveys the precise arrangement of atoms in the molecule, which is essential for understanding its chemical properties.

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Related Practice

Textbook Question

Label each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°).

(d)

Textbook Question

Label each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°).

(e)

(f)

Textbook Question

Correct the following incorrect names using standard IUPAC nomenclature. [Draw a compound that corresponds to the incorrect name, and then rename it.]

(e) 2,6-diethyl-1-methylcycloheptane

Textbook Question

Each of the following descriptions applies to more than one alkane. In each case, draw and name two structures that match the description.

e. a (2,3-dimethylpentyl)cycloalkane

Textbook Question

Draw the structure and give the molecular formula for each of the following compounds.

a. 1-ethyl-3-methylcycloheptane

b. isobutylcyclohexane

Textbook Question

Draw the structure and give the molecular formula for each of the following compounds.

e. 3-ethyl-2,4-dimethylhexane

f. 1,1-diethyl-4-(3,3-dimethylbutyl)cyclohexane